Oakland Vacations from $255
Book a Hotel + Flight or Car together to unlock savings
Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Save 100% on your flight
Price was $747, price is now $518 per person
$518
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
The hotel was beautiful, clean and the staff was super friendly.
Reviewed on Dec 18, 2025
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Save 100% on your flight
Price was $637, price is now $445 per person
$445
per person
Mar 5 - Mar 8
found 9 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Everyone I encountered was amazing through our experience related to our stay. There was an event occurring in the main entry way during our stay and the valet assisted us in locating parking, called the front desk and checked in from the door, they were very informative and helpful, even the building staff were very friendly and helpful helped us with the door on arrival. It would be nice to be able to use valet service, especially since it is paid parking anyways, and also enter through the nicer main lobby rather than a service entrance and padded frieght elevator... I did chose the Penn because of its prestige, location, amenities, and to view/enjoy craftsmanship of the architecture and chandilers specifically (as a former apprentice of the artist). Overall great stay.
Reviewed on Dec 9, 2025
Hotel Indigo Pittsburgh East Liberty by IHG
East Liberty
Price was $433, price is now $304 per person
$304
per person
Mar 5 - Mar 8
found 9 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
8/10 Very Good! (1,003 reviews)
Polite and friendly staff; Very clean hotel, all areas. Several dining option in walking distance. Trader Joe’s, Whole Foods, Market District grocery stores within a mile,
Reviewed on Dec 24, 2025
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $139 total per night from Dec 28 to Dec 29
$139 total
Dec 28 - Dec 29
Total with taxes and fees
8.8/10 Excellent! (547 reviews)
Room was so clean and everything was good
Reviewed on Dec 17, 2025
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
$171 nightly
The price is $195 total per night from Jan 1 to Jan 2
$195 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.2/10 Wonderful! (724 reviews)
Excellent
Reviewed on Dec 16, 2025
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundable
$118 nightly
The price is $135 total per night from Dec 28 to Dec 29
$135 total
Dec 28 - Dec 29
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
Very cute hotel with friendly staff. It was December so was decorated for Christmas in the lobby. Restaurant inside hotel was good as well. Bed was average and pillows were not the greatest but overall the hotel was excellent for the price and very close to traveling to the Steelers stadium, the ...
Reviewed on Dec 21, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Carnegie Museum of Natural History
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Things to do
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena
$102
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
Pittsburgh: Beauty of the Burgh Bike Tour
$59
per adult
94% of travellers recommend
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- University of Pittsburgh
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- Chatham University
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.